1,3-Bis(2-chloroethyl)urea → N,N'-Bis(2-chloroethyl)-N-nitrosourea

HRID 436913Notes

Reaction equation

HRID 436913 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][CH2:6][CH2:7][NH:8][C:9]([NH:11][CH2:12][CH2:13][Cl:14])=[O:10]>O.C(O)=O>[CH2:7]([NH:8][C:9]([N:11]([N:1]=[O:3])[CH2:12][CH2:13][Cl:14])=[O:10])[CH2:6][Cl:5]

Participants

5

Reactant 2

HCID 957911,3-Bis(2-chloroethyl)ureaHCID 23668193Sodium Nitrite

Product 1

HCID 2578N,N'-Bis(2-chloroethyl)-N-nitrosourea

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A cold solution of 0.2346 g (3.4 mmole) sodium nitrite in 2 ml water was slowly added to a stirred solution of 0.2727 g (1.47 mmole) 1,3-bis(2-chloroethyl)urea in 2 ml 88% formic acid at 0°. After 2 hours at 0°, 0.1449 g (46.0%) of an oil solid phase was removed. The ir spectrum of this fraction failed to agree with that of BCNU. After 2 days a small amount of crystalline BCNU slowly formed in this oil phase. A methylene dichloride extract of the aqueous phase yielded 0.0943 g (30.0%) of an amber oil whose ir spectrum agreed with that of a known sample of BCNU. Treatment of this oil with 5 ml hexane and cooling to 0° gave crystalline BCNU which formed an oil on warming to ambient temperature.

Workup

  1. custom0.1449 g (46.0%) of an oil solid phase was removed

Sources & evidence

ORD record
ord-ec2c27c6ed234677bca57165fa242cf5
Source dataset
uspto-grants-1977_06
Patent number
US04028410

Reaction notes

Loading…